# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound1
_database_code_depnum_ccdc_archive 'CCDC 1522200'
_audit_update_record             
;
2016-12-12 deposited with the CCDC.
2017-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 I4 N2 O4'
_chemical_formula_weight         810.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   14.1757(6)
_cell_length_b                   9.6136(3)
_cell_length_c                   17.0845(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.777(2)
_cell_angle_gamma                90
_cell_volume                     2306.85(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    8976
_cell_measurement_theta_min      3.21
_cell_measurement_theta_max      27.58

_exptl_crystal_description       parallelepide
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.335
_exptl_crystal_F_000             1492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    5.425
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.365
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrystalClear, Rigaku MSC, 2005'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
;
fine-focus sealed tube with graphite monochromator
;
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IPDS'
_diffrn_measurement_method       'θ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14491
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.207
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5000
_reflns_number_gt                4551
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear, Rigaku MSC, 2005'
_computing_cell_refinement       'CrystalClear, Rigaku MSC, 2005'
_computing_data_reduction        'CrystalClear, Rigaku MSC, 2005'
_computing_structure_solution    'CrystalClear, Rigaku MSC, 2005'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0234P)²+1.0336P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5000
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0557
_refine_ls_wR_factor_gt          0.0543
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.43796(2) 0.02083(2) 0.31199(2) 0.03304(6) Uani 1 1 d . . . . .
I2 I 0.34765(2) 0.05656(2) 0.14350(2) 0.03123(6) Uani 1 1 d . . . . .
I3 I 0.25244(2) 0.07515(2) -0.01409(2) 0.03870(7) Uani 1 1 d . . . . .
I4 I 0.65714(2) -0.03895(2) 0.26514(2) 0.03331(6) Uani 1 1 d . . . . .
N1 N 0.84206(18) 0.2958(2) 0.07078(13) 0.0259(5) Uani 1 1 d . . . . .
H1 H 0.8354 0.2048 0.0714 0.034 Uiso 1 1 calc R U . . .
O1 O 0.93292(17) 0.4695(2) 0.03347(13) 0.0316(5) Uani 1 1 d . . . . .
O2 O 0.56065(18) 0.5680(2) 0.21128(15) 0.0381(6) Uani 1 1 d . . . . .
C1 C 0.9756(2) 0.2348(3) 0.00307(17) 0.0337(7) Uani 1 1 d . . . . .
H1A H 0.9510 0.1414 0.0113 0.051 Uiso 1 1 calc R U . . .
H1B H 0.9741 0.2518 -0.0536 0.051 Uiso 1 1 calc R U . . .
H1C H 1.0413 0.2421 0.0294 0.051 Uiso 1 1 calc R U . . .
C2 C 0.9149(2) 0.3407(3) 0.03706(16) 0.0257(6) Uani 1 1 d . . . . .
C3 C 0.7722(2) 0.3721(3) 0.10656(15) 0.0232(6) Uani 1 1 d . . . . .
C4 C 0.7710(2) 0.5166(3) 0.11376(18) 0.0307(7) Uani 1 1 d . . . . .
C5 C 0.6992(2) 0.5786(3) 0.14960(19) 0.0322(7) Uani 1 1 d . . . . .
C6 C 0.6295(2) 0.4998(3) 0.17766(17) 0.0265(6) Uani 1 1 d . . . . .
C7 C 0.6313(2) 0.3554(3) 0.17048(18) 0.0311(7) Uani 1 1 d . . . . .
C8 C 0.7023(2) 0.2928(3) 0.13523(17) 0.0284(6) Uani 1 1 d . . . . .
N2 N 0.15197(18) 0.6837(2) 0.40990(14) 0.0261(5) Uani 1 1 d . . . . .
H2 H 0.1559 0.7735 0.4008 0.034 Uiso 1 1 calc R U . . .
O3 O 0.06736(16) 0.52199(19) 0.46476(13) 0.0294(5) Uani 1 1 d . . . . .
O4 O 0.44289(17) 0.3965(2) 0.29083(13) 0.0339(5) Uani 1 1 d . . . . .
C9 C 0.0118(3) 0.7579(3) 0.4644(2) 0.0380(8) Uani 1 1 d . . . . .
C10 C 0.0789(2) 0.6467(3) 0.44617(17) 0.0254(6) Uani 1 1 d . . . . .
C11 C 0.2251(2) 0.6020(3) 0.38323(15) 0.0220(5) Uani 1 1 d . . . . .
C12 C 0.2294(2) 0.4580(3) 0.38739(18) 0.0284(6) Uani 1 1 d . . . . .
C13 C 0.3029(2) 0.3892(3) 0.35669(18) 0.0285(6) Uani 1 1 d . . . . .
C14 C 0.3707(2) 0.4623(3) 0.32279(16) 0.0240(6) Uani 1 1 d . . . . .
C15 C 0.3671(2) 0.6066(3) 0.31975(17) 0.0276(6) Uani 1 1 d . . . . .
C16 C 0.2948(2) 0.6750(3) 0.35009(17) 0.0261(6) Uani 1 1 d . . . . .
H1O H 1.0000 0.5000 0.0000 0.10(2) Uiso 1 2 d S . P . .
H2O H 0.529(3) 0.516(4) 0.233(2) 0.044(11) Uiso 1 1 d . . . . .
H3O H 0.0000 0.5000 0.5000 0.08(2) Uiso 1 2 d S . P . .
H4 H 0.821(3) 0.576(3) 0.091(2) 0.041(10) Uiso 1 1 d . . . . .
H4O H 0.441(3) 0.318(4) 0.2924(19) 0.030(10) Uiso 1 1 d . . . . .
H5 H 0.700(2) 0.676(4) 0.1562(17) 0.032(9) Uiso 1 1 d . . . . .
H7 H 0.585(3) 0.303(3) 0.187(2) 0.040(9) Uiso 1 1 d . . . . .
H8 H 0.707(2) 0.185(3) 0.1294(15) 0.017(7) Uiso 1 1 d . . . . .
H9A H 0.039(4) 0.847(5) 0.463(3) 0.086(16) Uiso 1 1 d . . . . .
H9B H -0.048(4) 0.756(5) 0.434(3) 0.10(2) Uiso 1 1 d . . . . .
H9C H -0.004(3) 0.753(5) 0.511(3) 0.078(15) Uiso 1 1 d . . . . .
H12 H 0.179(2) 0.402(3) 0.4097(18) 0.028(8) Uiso 1 1 d . . . . .
H13 H 0.305(2) 0.294(3) 0.3575(17) 0.027(8) Uiso 1 1 d . . . . .
H15 H 0.413(2) 0.658(3) 0.2982(18) 0.033(9) Uiso 1 1 d . . . . .
H16 H 0.293(2) 0.779(3) 0.3527(16) 0.026(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I2 3.0077(3) . ?
I2 I3 2.8493(3) . ?
I4 I4 2.7509(4) 2_655 ?
N1 C2 1.321(4) . ?
N1 C3 1.434(3) . ?
N1 H1 0.8800 . ?
O1 C2 1.267(3) . ?
O1 H1O 1.210(2) . ?
O2 C6 1.365(3) . ?
O2 H2O 0.80(4) . ?
C1 C2 1.500(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C8 1.389(4) . ?
C3 C4 1.396(4) . ?
C4 C5 1.391(4) . ?
C4 H4 1.02(4) . ?
C5 C6 1.382(4) . ?
C5 H5 0.94(3) . ?
C6 C7 1.395(4) . ?
C7 C8 1.379(4) . ?
C7 H7 0.91(4) . ?
C8 H8 1.04(3) . ?
N2 C10 1.325(3) . ?
N2 C11 1.424(3) . ?
N2 H2 0.8800 . ?
O3 C10 1.256(3) . ?
O3 H3O 1.2143(19) . ?
O4 C14 1.377(3) . ?
O4 H4O 0.75(3) . ?
C9 C10 1.492(4) . ?
C9 H9A 0.94(5) . ?
C9 H9B 0.93(6) . ?
C9 H9C 0.86(4) . ?
C11 C12 1.387(4) . ?
C11 C16 1.393(4) . ?
C12 C13 1.395(4) . ?
C12 H12 1.00(3) . ?
C13 C14 1.380(4) . ?
C13 H13 0.91(3) . ?
C14 C15 1.388(4) . ?
C15 C16 1.377(4) . ?
C15 H15 0.94(3) . ?
C16 H16 1.00(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I3 I2 I1 175.845(9) . . ?
C2 N1 C3 130.1(2) . . ?
C2 N1 H1 115.0 . . ?
C3 N1 H1 115.0 . . ?
C2 O1 H1O 115.9(2) . . ?
C6 O2 H2O 112(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N1 121.0(2) . . ?
O1 C2 C1 120.9(3) . . ?
N1 C2 C1 118.0(3) . . ?
C8 C3 C4 119.8(2) . . ?
C8 C3 N1 115.9(2) . . ?
C4 C3 N1 124.3(2) . . ?
C5 C4 C3 118.9(3) . . ?
C5 C4 H4 121(2) . . ?
C3 C4 H4 120(2) . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 120.1(19) . . ?
C4 C5 H5 118.7(19) . . ?
O2 C6 C5 118.0(2) . . ?
O2 C6 C7 122.5(3) . . ?
C5 C6 C7 119.5(3) . . ?
C8 C7 C6 119.7(3) . . ?
C8 C7 H7 120(2) . . ?
C6 C7 H7 120(2) . . ?
C7 C8 C3 120.8(3) . . ?
C7 C8 H8 122.4(15) . . ?
C3 C8 H8 116.8(15) . . ?
C10 N2 C11 130.5(2) . . ?
C10 N2 H2 114.7 . . ?
C11 N2 H2 114.7 . . ?
C10 O3 H3O 115.5(2) . . ?
C14 O4 H4O 114(3) . . ?
C10 C9 H9A 112(3) . . ?
C10 C9 H9B 115(3) . . ?
H9A C9 H9B 110(4) . . ?
C10 C9 H9C 114(3) . . ?
H9A C9 H9C 104(4) . . ?
H9B C9 H9C 101(4) . . ?
O3 C10 N2 120.8(3) . . ?
O3 C10 C9 121.5(3) . . ?
N2 C10 C9 117.7(3) . . ?
C12 C11 C16 119.7(2) . . ?
C12 C11 N2 124.2(2) . . ?
C16 C11 N2 116.1(2) . . ?
C11 C12 C13 118.9(2) . . ?
C11 C12 H12 121.8(18) . . ?
C13 C12 H12 119.3(18) . . ?
C14 C13 C12 121.0(2) . . ?
C14 C13 H13 119.1(19) . . ?
C12 C13 H13 120.0(19) . . ?
O4 C14 C13 122.0(2) . . ?
O4 C14 C15 118.0(2) . . ?
C13 C14 C15 120.0(2) . . ?
C16 C15 C14 119.2(2) . . ?
C16 C15 H15 119.2(19) . . ?
C14 C15 H15 121.5(19) . . ?
C15 C16 C11 121.2(2) . . ?
C15 C16 H16 121.1(17) . . ?
C11 C16 H16 117.5(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O1 1.210(2) 1.210(2) 2.420(4) 180.00(17) 3_765
O2 H2O O4 0.80(4) 2.02(4) 2.822(3) 175(4) .
O4 H4O I1 0.75(3) 2.88(3) 3.631(2) 175(3) .
N1 H1 I3 0.88 3.07 3.885(2) 155.1 3_655
N2 H2 I2 0.88 2.82 3.699(2) 173.4 2_565

_refine_diff_density_max         1.593
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.119

_shelxl_version_number           2014/6

# start Validation Reply Form


_vrf_PLAT434_compound1           
;
Problem: Short Inter HL..HL Contact I1     ..  I4      ..       3.36 Ang.   

RESPONSE: Based on bibliographic data (P.H. Svensson, L. Kloo,
Chem. Rev, 2003, 103, 1649-1684) this I...I distance is 
considered as secondary  bond. 

;



